Patents Represented by Attorney G. R. Plotecher
  • Patent number: 4086253
    Abstract: 3,3',5,5'-Tetra-substituted diphenoquinone, such as 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone, is efficiently prepared by a process comprising contacting oxygen with a liquid 2,6-disubstituted phenol, such as 2,6-di-t-butylphenol in the presence of aqueous base and a catalytic amount of a phase-transfer catalyst, such as tri-n-butylmethylammonium chloride. This process is characterized by high yields, short reaction times and facile product recovery.
    Type: Grant
    Filed: July 8, 1976
    Date of Patent: April 25, 1978
    Assignee: The Dow Chemical Company
    Inventors: Charles R. Hopper, Larry D. Kershner
  • Patent number: 4079075
    Abstract: The process of oxidizing organic compounds by dissolving the organic compound in a water-immiscible, inert organic solvent and contacting same with an aqueous hypohalite ion in the presence of a catalytic amount of a quaternary onium salt is improved by employing a primary alkyl ester as the organic solvent. For example, cyclohexylmethylamine is oxidized under mild conditions to a high yield of cyclohexylnitrile by dissolving the amine in ethyl acetate and contacting same with aqueous hypochlorite and in the presence of a catalytic amount of tetra-n-butylammonium chloride.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: March 14, 1978
    Assignee: The Dow Chemical Company
    Inventors: George A. Lee, Harold H. Freedman
  • Patent number: 4075394
    Abstract: Tannin migration in tannin-containing wood substrates, such as redwood and cedar, is inhibited by treating said substrate with an aqueous solution of polyalkylenimine, such as polyethylenimine.
    Type: Grant
    Filed: April 8, 1976
    Date of Patent: February 21, 1978
    Assignee: The Dow Chemical Company
    Inventor: Victor E. Meyer
  • Patent number: 4070354
    Abstract: Aziridinyl-terminated polymers containing the recurring unit ##STR1## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is hydrogen or a side chain of like structure, are prepared by warming N-(2-hydroxyethyl)- or N-(2-hydroxypropyl)ethylenimine or -propyleneimine. Generally, the reaction is conducted in the presence of an alkali metal and at least trace amounts of water. The polymers are useful as curing agents for epoxy resins.
    Type: Grant
    Filed: September 28, 1972
    Date of Patent: January 24, 1978
    Assignee: The Dow Chemical Company
    Inventors: Clarence R. Dick, James Larry Potter
  • Patent number: 4067921
    Abstract: C.sub.n dienes are efficiently separated and produced from a C.sub.n hydrocarbon feed stream, wherein n is 4-8. For example, 1,2- and 1,3-butadienes are separated and produced from a C.sub.4 hydrocarbon feed stream comprising C.sub.4 alkynes, n- and isobutenes, n- and isobutanes and 1,2- and 1,3-butadienes by sequentially:A. hydrogenating the C.sub.4 alkynes and removing any heavy residue produced thereby;B. separating the 1,2- and 1,3-butadienes into a first stream and the remaining C.sub.4 hydrocarbons into a second stream;C. removing first the isobutene and second the n- and isobutanes from the second stream; andD. converting the remaining alkenes of the second stream to 1,2- and 1,3-butadienes and then recycling said butadienes to the first stream of (b).This process affords greater product flexibility with less physical plant than that afforded by conventional processes.
    Type: Grant
    Filed: December 6, 1976
    Date of Patent: January 10, 1978
    Assignee: The Dow Chemical Company
    Inventor: Gunnar I. Helberg
  • Patent number: 4061682
    Abstract: Symmetrical ethers are prepared in high yield by reacting an alkyl halide, sulfate, or sulfonate with base in the presence of a catalytic amount of both an onium salt and a carboxylate salt. For example, dibenzyl ether is produced in yields exceeding 95 percent by contacting benzylchloride with a 50 percent sodium hydroxide solution in the presence of a catalytic amount of both tetra-n-butylammonium bisulfate and sodium acetate.
    Type: Grant
    Filed: July 23, 1975
    Date of Patent: December 6, 1977
    Assignee: The Dow Chemical Company
    Inventors: Robert A. Dubois, Harold H. Freedman
  • Patent number: 4054533
    Abstract: Heat transfer fluids consisting essentially of about, by weight:A. 20 to about 40 percent diphenyl ether;B. 40 to about 60 percent of a 2-biphenylylphenyl ether (2-bippe) and 4-biphenylylphenyl ether (4-bippe) mixture at a 2-bippe:4-bippe weight ratio of at least about 2:1; andC. 12 to about 25 percent of a polyphenylphenol mixtureExhibit freeze points of -18.degree. C or less. These heat transfer fluids have excellent fluidity over a broad temperature range and display unexpectedly good thermal stability.
    Type: Grant
    Filed: June 24, 1976
    Date of Patent: October 18, 1977
    Assignee: The Dow Chemical Company
    Inventor: William David Watson
  • Patent number: 4054602
    Abstract: Bis-chloromethyl ether is efficiently removed from chloroacetyl chloride by a process comprising contacting the chloroacetyl chloride containing generally about 100 to about 250 ppm bis-chloromethyl ether with hydrochloric acid at a temperature between about 30.degree. C and about 160.degree. C in the presence of a catalytic amount of a Lewis or strong protic acid, such as aluminum chloride or oleum. After a contact time of about 1 hour, the chloroacetyl chloride contains less than 0.3 ppm bis-chloromethyl ether.
    Type: Grant
    Filed: September 30, 1976
    Date of Patent: October 18, 1977
    Assignee: The Dow Chemical Company
    Inventor: Yog R. Dhingra
  • Patent number: 4049849
    Abstract: Leaching of a fire retardant salt, such as a mixture of ammonium phosphates, impregnated into a wood substrate is inhibited by a process comprising:A. impregnating the wood substrate with an aqueous solution of a cyclic sulfonium zwitterion (CSZ), exemplified by structural formula (I), andB. curing the resulting CSZ-impregnated wood substrate. ##STR1## CSZ impregnation of the wood substrate can be either concurrent with or subsequent to the fire retardant salt impregnation of same. This process provides a significant degree of leach protection to otherwise very leachable fire retardant salts.
    Type: Grant
    Filed: April 14, 1976
    Date of Patent: September 20, 1977
    Assignee: The Dow Chemical Company
    Inventor: Frederick L. Brown
  • Patent number: 4045410
    Abstract: Novel copolymer resins having the repeating unit ##STR1## WHEREIN EACH R is independently alkyl of 1 to about 10 carbon atoms or halogen, z is oxygen or sulfur, the dashed line is an optional chemical bond, the group represented by z taken with the dashed line represents dibenzofuran and dibenzothiophene moieties, or mixtures thereof, each R" is hydrogen or ##STR2## wherein each R' is a hydrocarbon or substituted hydrocarbon radical of from 2 to about 11 carbon atoms, n averages about 3-10, each m is 0-2 and p and q are each 0 or 1 with the proviso that the sum of p and q has an average value of 0.1-1.0 and there is an average of at least one carboxyl group per polymer molecule, are prepared by reacting a mixture comprising a hydroxymethylated diphenylether-formaldehyde copolymer with an anhydride of the formula ##STR3## wherein R' is a hydrocarbon or substituted hydrocarbon radical of from 2 to about 11 carbon atoms, at a temperature between about 120.degree. and about 170.degree. C.
    Type: Grant
    Filed: October 17, 1975
    Date of Patent: August 30, 1977
    Assignee: The Dow Chemical Company
    Inventor: Raymond A. Plepys
  • Patent number: 4043960
    Abstract: Aqueous dispersions comprising:A. a thermosetting hydroxy-functional condensation copolymer, such as the copolymer of diphenyl oxide and formaldehyde;B. a curing amount of curing agent, such as acid-catalyzed hexamethoxymethylmelamine; andC. an aqueous polyvinyl alcohol, have good shelf stability.
    Type: Grant
    Filed: January 19, 1976
    Date of Patent: August 23, 1977
    Assignee: The Dow Chemical Company
    Inventors: Paul Joseph Kress, Raymond A. Plepys
  • Patent number: 4001293
    Abstract: A new process for preparing .gamma.-halonitriles comprising reacting by contacting a 1,3-dihalopropane, such as 1-chloro-3-bromopropane, or mixtures thereof, such as 1-chloro-3-bromopropane and 1-chloro-3-iodopropane, with an alkali metal cyanide, such a sodium cyanide, in the presence of an onium salt, such as benzyltriethylammonium chloride, and an alkali metal halide, such as sodium chloride. The .gamma.-halonitriles are useful in preparing cyclopropylcyanide, a herbicide intermediate.
    Type: Grant
    Filed: April 2, 1975
    Date of Patent: January 4, 1977
    Assignee: The Dow Chemical Company
    Inventors: James H. Plonka, Ralph A. Davis
  • Patent number: 4001107
    Abstract: Morpholinones are efficient selective solvents for aromatic hydrocarbons from hydrocarbon mixtures containing same. For example, N-methyl-3-morpholinone is an efficient selective solvent for benzene, toluene, and xylene from a hydrocarbon stream obtained from a catalytic reformer.
    Type: Grant
    Filed: June 18, 1975
    Date of Patent: January 4, 1977
    Assignee: The Dow Chemical Company
    Inventors: John W. Bozzelli, George D. Shier
  • Patent number: 3996204
    Abstract: Novel N-(m or p-vinylbenzyl)aziridines are disclosed which correspond to the structural formula ##EQU1## wherein R and R' are hydrogen or lower alkyl. They are highly reactive difunctional monomers which can be homopolymerized or copolymerized to form many useful polymers.
    Type: Grant
    Filed: February 19, 1974
    Date of Patent: December 7, 1976
    Assignee: The Dow Chemical Company
    Inventors: Donald A. Tomalia, Jerry D. DeVrieze
  • Patent number: 3996259
    Abstract: Organic compounds oxidizable by hypohalite ion, such as amines, amides, primary and secondary alcohols, and alkanals are efficiently oxidized in a biphasic mixture comprising:A. a water immiscible, liquid organic phase comprising an organic compound oxidizable by hypohalite ion; withB. an aqueous phase containing hypohalite ion; andC. a catalytic amount of a quaternary ammonium salt and/or a quaternary phosphonium salt.
    Type: Grant
    Filed: November 6, 1975
    Date of Patent: December 7, 1976
    Assignee: The Dow Chemical Company
    Inventors: George A. Lee, Harold H. Freedman
  • Patent number: 3966626
    Abstract: Heat transfer agents containing at least about 20 volume percent of diphenyl oxide and at least 20 volume percent of diphenylyl phenyl ether, polyphenyl ether or mixtures thereof have been found to be excellent heat transfer fluids with an unexpectedly broad range of liquidity.
    Type: Grant
    Filed: September 17, 1973
    Date of Patent: June 29, 1976
    Assignee: The Dow Chemical Company
    Inventors: Larry L. Jackson, Walter F. Seifert, Daniel E. Collins